Events The 9th International Electronic Conference on Synthetic Organic Chemistry

Event submissions

Published

This submission belongs to the session a. General Organic Synthesis of the event The 9th International Electronic Conference on Synthetic Organic Chemistry

Published date

01 Nov, 2005

Citation

Cherif Behloul, David Guijarro, Miguel Yus, Reductive Deprotection of Boc-Protected Alcohols, Amines and Thiols via a DTBB-Catalysed Lithiation Process, in Proceedings of The 9th International Electronic Conference on Synthetic Organic Chemistry, 1 November–30 November 2005, MDPI: Basel, Switzerland, doi: 10.3390/ecsoc-9-01467

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Reductive Deprotection of Boc-Protected Alcohols, Amines and Thiols via a DTBB-Catalysed Lithiation Process

Cherif Behloul ¹

David Guijarro ¹

Miguel Yus ¹

1. Departamento de Química Orgánica, Facultad de Ciencias and Instituto de Síntesis Orgánica (ISO), Universidad de Alicante, Apdo. 99, 03080 Alicante, Spain

Abstract

The DTBB-catalysed lithiation of Boc-protected alcohols, amines and thiols in THF at 0ºC led, after quenching with methanol, to the recovery of the free alcohols, amines and thiols in short reaction times and with very good yields. The procedure has been applied to primary, secondary and tertiary alcohols, secondary amines and a primary thiol. This method represents a reasonable alternative to the previously reported deprotection procedures.

Keywords

lithium

DTBB

tert-butoxycarbonyl

Boc

deprotection

alcohols

amines

thiols

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